50 Questions to Ask Yourself after 6 Months of Freelancing

It’s a well-known fact that most freelancers don’t get performance reviews.

For one thing, most private clients don’t think of it. Even on bidding sites where clients can rate a freelancer, the ratings are not really that helpful. They just indicate whether a client was satisfied.

There’s no reason why you, as a freelancer, can’t review your own performance. In fact, conducting a self-review from to time is a really good idea.

In this post, I share fifty questions that you can answer on your own to evaluate your freelancing business.

Be sure to wait a while so that you have enough information to evaluate your freelancing business fairly before doing this (six months is about right). You can revisit these questions periodically (again, six months is about right).

Use this questionnaire to get a snapshot of where your freelancing business is and to find areas you need to change or strengthen. Of course, these questions are just a guideline. You’ll develop your own “performance review” questions over time.

Questions about Your Work Quality

Quality work is very important as you attempt to distinguish yourself from the competition. Here are some questions to help you discover whether your work quality is adequate:

Are you proud of the projects that you’ve recently completed? Having pride in your work is an important element of being satisfied with what you do.

Do you feel that projects that you work on represent your best work? Occasionally, first-time freelancers are forced to take on projects that don’t really reflect their abilities. However, you should be able to move past this point.

If you had to do your recent projects again, what would you do differently? It’s a good idea to reflect on your recent work and make notes of any areas that need improvement.

Have you done any projects that you would be willing to add to your portfolio? You should be constantly building and enhancing your professional portfolio with your most recent work.

What project did you enjoy the most? If there was a project that you particularly enjoyed, it may be a good idea to look for similar projects.

What project did you find the most challenging? If a project was particularly difficult, it’s important to find out why.

What have your clients said about your work? Client feedback can be invaluable. If your clients haven’t provided any, don’t be afraid to ask.

Are you getting any repeat business or referrals from clients? If your clients give you repeat business or refer others to you, there’s a good chance that they are satisfied.

Questions about Your Freelancing Finances

As a businessperson, your goal is to make a profit. These are the tough questions to help you evaluate your finances:

Are you making ends meet as a freelancer? In the end, making a living is what freelancing is about. Are you?

Do you have multiple clients? It’s never a good idea to build your freelancing business upon work from a single client.

Do you keep track of all of your income and expenses? You will need these records for income tax purposes and as your business expands.

Are you saving for taxes or paying quarterly? One of the biggest shocks for many new freelancers is the size of their tax liability for their first year of business.

Do you have an emergency fund? It’s a good idea to have several months’ worth of expenses set aside for emergencies.

Are your rates competitive with others in your industry? If your rates are too high or too low, it may be time to make some adjustments.

Do you charge for extras such as rush work or scope creep? If you don’t charge for these client services, you may wish to consider doing so.

When was the last time you raised your rates? Ultimately, you are in charge of what you earn. You can ask whatever the market will bear for your services.

Questions about Your Freelancing Lifestyle

One of the aspects of freelancing that draws many is the freelancing lifestyle. Here is how you can determine whether the lifestyle is working:

How many times have you worked overtime in the past six months? If you are working too many hours, you may be at risk of burning out.

Do you keep regular business hours? Generally, it’s a good policy to set aside some regular hours during which clients can contact you.

Do you have enough work to keep you busy? If times are slow, don’t stop marketing.

Have you been able to take any personal time off? Again, if you are unable to take time off when you need a break or are sick, you may be at risk for burnout.

How often do family concerns interrupt your project work? Freelancers often struggle to balance family and work.

How often does project work interrupt quality time with your friends and family? Quality time with your friends and family is important to your long-term happiness. Don’t neglect it.

Is your work environment comfortable? You will spend a lot of time in your workspace. Make sure it is comfortable.

Are you equipped to work and travel? Do you have the tools to work on the road? There are more and more opportunities for freelancers to work and travel.

Questions about Your Skills and Tools

To run a successful business, you must keep your skills and tools up to date. These questions will help:

Have you learned anything new about your field recently? No matter what your field is, there are new developments almost every day. Keep up.

Do you feel your current skills are up to date? Be honest. Are your skills really up to date?

Is there an area of your field that you need to learn more about? There are plenty of resources available to help you learn more.

Is your current software up to date? Outdated software can really hold you back.

Do you have all of the software that you need? Make sure you have what you need to succeed.

Is your computer equipment adequate? You should have a budget for upgrading your computer equipment regularly.

Is your Internet connection fast enough? As a businessperson, you need a fairly high-speed connection.

Is your phone system adequate for your business needs? You may find that you need a second line for your business.

Questions about Your Business Network

For many freelancers most of their clients come through networking. Here are some questions to evaluate your networking efforts:

Are you involved in social media? If you answered “no,” you may be missing many opportunities.

Does your social media presence include the big three (Facebook, LinkedIn, and Twitter)? The big three are probably the most popular social media platforms.

Does your business have an online presence? An online presence is expected of a freelancer.

Do you have a blog or website? A great way to get an online presence is to have a home site, either a blog or website, that you control.

Are you regularly taking part in local networking opportunities? Don’t overlook local businesses in your attempts to find clients.

Do you have good relationships with others (offline or online) in your field? Business is based on trust and trust comes from relationships.

Do you have a mailing list, newsletter, or other means of keeping in touch with prospects? Typically, it takes more than one contact for a prospect to become a client.

Has your networking netted you any work? One way to tell if your networking is working is whether it has gotten you clients.

Do you refer work to others? If you refer work to others, they may be more likely to refer work to you.

Do you take advantage of advertising? Advertising may be a traditional form of marketing, but it still works. Advertising in local publications is often reasonably priced.

Questions about Your Goals

Like any business, your freelancing business should have goals. Here are some questions to help:

Has freelancing lived up to your expectations? Nearly everyone finds that the reality of freelancing is somewhat different than they thought it would be.

Are you happy doing what you are doing? Happiness is the key. If you are unhappy as a freelancer, it will eventually affect your work.

If you could change anything, what would you change about your business? Well, why not take steps to make the change?

What courses or books would help you to grow as a freelancer? Set aside a budget for personal growth.

Where do you see your freelancing business in a year? In five years? This is a good way to identify your goals.

What steps do you need to take to get from where your business is now to where you want to be? Develop a plan to achieve your long-range goals.

What’s next for your business? This is probably a good indication of your short-range goals.

What’s next for you personally? Your personal goals and business goals should complement each other if possible.

Your Turn

How do you evaluate your freelancing business? What questions would you add?

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